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Abstract
Benzophenone (1), diphenyl sulfone, and 4-nitro-2′-chloro- and 4-nitro-2′,6′-dichloro-diphenyl ethers (23,24) have been chlorosulfonated. The direct yield of benzophenone-3,3′-disulfonyl chloride (2) was low, the majority of product was the disulfonic acid. Diphenyl sulfone (11) with a large amount of chlorosulfonic acid (8 mols) at 140° gave the 3,3′-disulfonyl chloride (12). With less reagent (6 mols) at 90° a mixture of the 3-sulfonyl chloride (21) and diphenyl sulfone was formed. Subsequent reaction with sodium azide gave the 3-sulfonyl azide (22). The diphenyl ether sulfonyl chlorides (25,26) were very susceptible to hydrolysis, especially (26) which probably accounts for the low yield obtained (31%). The various sulfonyl chlorides were characterized as amides, azides, hydrazides and hydrazones (Tables I-III) and their i.r., n.m.r., and mass spectral data are included.